AU2007296563B2 - Substituted amides, method of making, and method of use thereof - Google Patents

Substituted amides, method of making, and method of use thereof Download PDF

Info

Publication number: AU2007296563B2
Authority: AU; Australia
Prior art keywords: optionally substituted; chosen; alkyl; compound; formula
Prior art date: 2006-09-11
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Ceased

Application number

AU2007296563A

Other languages

English (en)

Other versions

AU2007296563A1 (en

Inventor

Peter A. Blomgren

Seung H. Lee

Scott A. Mitchell

Aaron C. Schmitt

Jianjun Xu

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Gilead Connecticut Inc

Original Assignee

Gilead Connecticut Inc

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2006-09-11

Filing date

2007-09-11

Publication date

2013-01-10

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=39184519&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=AU2007296563(B2) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

2007-09-11 Application filed by Gilead Connecticut Inc filed Critical Gilead Connecticut Inc

2008-03-20 Publication of AU2007296563A1 publication Critical patent/AU2007296563A1/en

2012-09-06 Assigned to GILEAD CONNECTICUT, INC. reassignment GILEAD CONNECTICUT, INC. Alteration of Name(s) of Applicant(s) under S113 Assignors: CGI PHARMACEUTICALS, INC.

2013-01-10 Application granted granted Critical

2013-01-10 Publication of AU2007296563B2 publication Critical patent/AU2007296563B2/en

Status Ceased legal-status Critical Current

2027-09-11 Anticipated expiration legal-status Critical

Links

238000000034 method Methods 0.000 title claims abstract description 52
238000004519 manufacturing process Methods 0.000 title claims description 10
150000001408 amides Chemical class 0.000 title description 4
150000001875 compounds Chemical class 0.000 claims abstract description 198
239000000203 mixture Substances 0.000 claims abstract description 99
230000000694 effects Effects 0.000 claims abstract description 70
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 68
201000010099 disease Diseases 0.000 claims abstract description 48
150000003839 salts Chemical class 0.000 claims abstract description 41
230000005764 inhibitory process Effects 0.000 claims abstract description 39
239000000651 prodrug Substances 0.000 claims abstract description 32
229940002612 prodrug Drugs 0.000 claims abstract description 32
239000012453 solvate Substances 0.000 claims abstract description 31
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 26
239000002671 adjuvant Substances 0.000 claims abstract description 8
239000000546 pharmaceutical excipient Substances 0.000 claims abstract description 8
239000000969 carrier Substances 0.000 claims abstract description 7
125000000217 alkyl group Chemical group 0.000 claims description 253
-1 4,5,6,7 tetrahydrobenzo[b]thiophen-2-yl Chemical group 0.000 claims description 92
229910052739 hydrogen Inorganic materials 0.000 claims description 74
239000001257 hydrogen Substances 0.000 claims description 73
125000001072 heteroaryl group Chemical group 0.000 claims description 64
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 57
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 48
125000003545 alkoxy group Chemical group 0.000 claims description 46
125000005843 halogen group Chemical group 0.000 claims description 43
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 35
125000001424 substituent group Chemical group 0.000 claims description 35
150000002431 hydrogen Chemical class 0.000 claims description 32
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 32
125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 30
125000003107 substituted aryl group Chemical group 0.000 claims description 27
206010028980 Neoplasm Diseases 0.000 claims description 22
208000010668 atopic eczema Diseases 0.000 claims description 22
208000023275 Autoimmune disease Diseases 0.000 claims description 20
230000000172 allergic effect Effects 0.000 claims description 20
201000011510 cancer Diseases 0.000 claims description 20
208000035475 disorder Diseases 0.000 claims description 20
125000004093 cyano group Chemical group *C#N 0.000 claims description 19
208000027866 inflammatory disease Diseases 0.000 claims description 19
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 19
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 19
238000011282 treatment Methods 0.000 claims description 19
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
125000000547 substituted alkyl group Chemical group 0.000 claims description 16
206010061218 Inflammation Diseases 0.000 claims description 15
230000004054 inflammatory process Effects 0.000 claims description 15
229910052757 nitrogen Inorganic materials 0.000 claims description 15
230000001154 acute effect Effects 0.000 claims description 14
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 12
239000003814 drug Substances 0.000 claims description 11
125000005842 heteroatom Chemical group 0.000 claims description 11
125000002252 acyl group Chemical group 0.000 claims description 8
125000005415 substituted alkoxy group Chemical group 0.000 claims description 7
125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 6
125000003396 thiol group Chemical group [H]S* 0.000 claims description 6
125000003373 pyrazinyl group Chemical group 0.000 claims description 5
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims description 4
125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 4
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 4
125000002098 pyridazinyl group Chemical group 0.000 claims description 4
125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
208000004736 B-Cell Leukemia Diseases 0.000 claims description 3
208000003950 B-cell lymphoma Diseases 0.000 claims description 3
125000003386 piperidinyl group Chemical group 0.000 claims description 3
125000004076 pyridyl group Chemical group 0.000 claims description 3
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 2
150000005829 chemical entities Chemical class 0.000 abstract description 94
210000003719 b-lymphocyte Anatomy 0.000 abstract description 43
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 72
210000004027 cell Anatomy 0.000 description 39
125000001188 haloalkyl group Chemical group 0.000 description 36
125000003118 aryl group Chemical group 0.000 description 33
ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 30
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
125000000753 cycloalkyl group Chemical group 0.000 description 23
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 20
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 19
238000006243 chemical reaction Methods 0.000 description 19
CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 18
125000004432 carbon atom Chemical group C* 0.000 description 18
SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 18
239000000243 solution Substances 0.000 description 18
238000003556 assay Methods 0.000 description 17
125000005037 alkyl phenyl group Chemical group 0.000 description 16
230000001363 autoimmune Effects 0.000 description 16
208000024891 symptom Diseases 0.000 description 16
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239000003981 vehicle Substances 0.000 description 15
108091000080 Phosphotransferase Proteins 0.000 description 14
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238000012360 testing method Methods 0.000 description 14
239000013543 active substance Substances 0.000 description 13
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XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 12
238000009472 formulation Methods 0.000 description 12
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
KRUDZWOELKQDJW-UHFFFAOYSA-N 3-amino-5-bromo-1-methylpyridin-2-one Chemical compound CN1C=C(Br)C=C(N)C1=O KRUDZWOELKQDJW-UHFFFAOYSA-N 0.000 description 11
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 11
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
239000002246 antineoplastic agent Substances 0.000 description 11
125000004435 hydrogen atom Chemical group [H]* 0.000 description 11
KZNVPAGYKJFYJE-UHFFFAOYSA-N n-[3-(5-amino-1-methyl-6-oxopyridin-3-yl)-2-methylphenyl]-4-tert-butylbenzamide Chemical compound C1=CC=C(C2=CN(C)C(=O)C(N)=C2)C(C)=C1NC(=O)C1=CC=C(C(C)(C)C)C=C1 KZNVPAGYKJFYJE-UHFFFAOYSA-N 0.000 description 11
239000000047 product Substances 0.000 description 11
239000011734 sodium Substances 0.000 description 11
125000002947 alkylene group Chemical group 0.000 description 10
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HQZPPIHPNFQMBY-UHFFFAOYSA-N 4-tert-butyl-n-[2-methyl-3-[1-methyl-5-[(6-morpholin-4-ylpyridazin-3-yl)amino]-6-oxopyridin-3-yl]phenyl]benzamide Chemical compound C1=CC=C(C2=CN(C)C(=O)C(NC=3N=NC(=CC=3)N3CCOCC3)=C2)C(C)=C1NC(=O)C1=CC=C(C(C)(C)C)C=C1 HQZPPIHPNFQMBY-UHFFFAOYSA-N 0.000 description 9
125000004429 atom Chemical group 0.000 description 9
238000002360 preparation method Methods 0.000 description 9
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KQUUWIXTVSGRAE-UHFFFAOYSA-N 4-tert-butyl-n-[2-methyl-3-[5-[(6-morpholin-4-ylpyridazin-3-yl)amino]-6-oxo-1h-pyridin-3-yl]phenyl]benzamide Chemical compound C1=CC=C(C=2C=C(NC=3N=NC(=CC=3)N3CCOCC3)C(=O)NC=2)C(C)=C1NC(=O)C1=CC=C(C(C)(C)C)C=C1 KQUUWIXTVSGRAE-UHFFFAOYSA-N 0.000 description 8
102000004190 Enzymes Human genes 0.000 description 8
108090000790 Enzymes Proteins 0.000 description 8
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
239000003795 chemical substances by application Substances 0.000 description 8
230000003993 interaction Effects 0.000 description 8
239000003755 preservative agent Substances 0.000 description 8
AOJAJTJZSBVNPU-UHFFFAOYSA-N 3,5-dibromo-1-methylpyridin-2-one Chemical compound CN1C=C(Br)C=C(Br)C1=O AOJAJTJZSBVNPU-UHFFFAOYSA-N 0.000 description 7
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
210000001744 T-lymphocyte Anatomy 0.000 description 7
239000012267 brine Substances 0.000 description 7
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102000004169 proteins and genes Human genes 0.000 description 7
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HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 7
235000010356 sorbitol Nutrition 0.000 description 7
239000000600 sorbitol Substances 0.000 description 7
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
HHWVGCPQQVCQFI-UHFFFAOYSA-N 4-tert-butyl-n-[3-[6-methoxy-5-[(6-morpholin-4-ylpyridazin-3-yl)amino]pyridin-3-yl]-2-methylphenyl]benzamide Chemical compound COC1=NC=C(C=2C(=C(NC(=O)C=3C=CC(=CC=3)C(C)(C)C)C=CC=2)C)C=C1NC(N=N1)=CC=C1N1CCOCC1 HHWVGCPQQVCQFI-UHFFFAOYSA-N 0.000 description 6
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 6
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XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 6
108060003951 Immunoglobulin Proteins 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
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NHXBEQAKGRHNII-UHFFFAOYSA-N n-[3-(5-amino-6-methoxypyridin-3-yl)-2-methylphenyl]-4-tert-butylbenzamide Chemical compound C1=C(N)C(OC)=NC=C1C1=CC=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)C)=C1C NHXBEQAKGRHNII-UHFFFAOYSA-N 0.000 description 6
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Classifications

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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
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- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Public Health (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Immunology (AREA)
Pulmonology (AREA)
Oncology (AREA)
Transplantation (AREA)
Hematology (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Neurology (AREA)
Orthopedic Medicine & Surgery (AREA)
Physical Education & Sports Medicine (AREA)
Otolaryngology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Medicinal Preparation (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Investigating Or Analysing Biological Materials (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

AU2007296563A 2006-09-11 2007-09-11 Substituted amides, method of making, and method of use thereof Ceased AU2007296563B2 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US84383306P	2006-09-11	2006-09-11
US60/843,833		2006-09-11
PCT/US2007/078185 WO2008033857A2 (fr)	2006-09-11	2007-09-11	Amides substitués, procédé de production et d'utilisation desdits amides

Publications (2)

Publication Number	Publication Date
AU2007296563A1 AU2007296563A1 (en)	2008-03-20
AU2007296563B2 true AU2007296563B2 (en)	2013-01-10

Family

ID=39184519

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
AU2007296563A Ceased AU2007296563B2 (en)	2006-09-11	2007-09-11	Substituted amides, method of making, and method of use thereof

Country Status (24)

Country	Link
EP (1)	EP2079726B1 (fr)
JP (1)	JP5563301B2 (fr)
KR (1)	KR101444481B1 (fr)
CN (1)	CN101605778A (fr)
AR (1)	AR063707A1 (fr)
AT (1)	ATE496909T1 (fr)
AU (1)	AU2007296563B2 (fr)
BR (1)	BRPI0716914A2 (fr)
CA (1)	CA2661951C (fr)
CL (1)	CL2007002642A1 (fr)
CO (1)	CO6180464A2 (fr)
CR (1)	CR10709A (fr)
DE (1)	DE602007012281D1 (fr)
EC (1)	ECSP099238A (fr)
ES (1)	ES2363269T3 (fr)
IL (1)	IL197264A0 (fr)
MA (1)	MA31276B1 (fr)
MX (1)	MX2009002651A (fr)
NO (1)	NO20091426L (fr)
PE (1)	PE20081370A1 (fr)
RU (1)	RU2009113692A (fr)
TW (1)	TWI398439B (fr)
WO (1)	WO2008033857A2 (fr)
ZA (1)	ZA200901634B (fr)

Families Citing this family (50)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AR063706A1 (es) *	2006-09-11	2009-02-11	Cgi Pharmaceuticals Inc	Determinadas amidas sustituidas, el uso de las mismas para el tratamiento de enfermedades mediadas por la inhibicion de la actividad de btk y composiciones farmaceuticas que las comprenden.
CA2701275C (fr)	2007-10-23	2016-06-21	F. Hoffmann-La Roche Ag	Inhibiteurs de kinase
US7683064B2 (en)	2008-02-05	2010-03-23	Roche Palo Alto Llc	Inhibitors of Bruton's tyrosine kinase
WO2009137596A1 (fr) *	2008-05-06	2009-11-12	Cgi Pharmaceuticals, Inc.	Amides substitués, leur méthode de préparation et d'utilisation en tant qu'inhibiteurs de btk
NZ601700A (en)	2008-06-24	2013-02-22	Hoffmann La Roche	5-phenyl-1H-pyridin-2-one and 6-phenyl-2H-pyridazin-3-one derivatives as inhibitors of Bruton's Tyrosine Kinase (Btk)
PL2300459T3 (pl)	2008-07-02	2013-10-31	Hoffmann La Roche	Nowe fenylopirazynony jako inhibitory kinazy
US8299077B2 (en)	2009-03-02	2012-10-30	Roche Palo Alto Llc	Inhibitors of Bruton's tyrosine kinase
AR082590A1 (es)	2010-08-12	2012-12-19	Hoffmann La Roche	Inhibidores de la tirosina-quinasa de bruton
KR20150032340A (ko)	2012-07-24	2015-03-25	파마시클릭스, 인코포레이티드	브루톤 티로신 키나제(btk)의 억제제에 대한 내성과 관련된 돌연변이
SMT201700160T1 (it)	2013-04-25	2017-05-08	Beigene Ltd	Composti eterociclici fusi come inibitori di protein chinasi
CN104177338B (zh) *	2013-05-22	2018-04-03	南京勇山生物科技有限公司	一类布鲁顿激酶抑制剂
ES2792183T3 (es)	2013-09-13	2020-11-10	Beigene Switzerland Gmbh	Anticuerpos anti-PD1 y su uso como productos terapéuticos y de diagnóstico
KR101813830B1 (ko) *	2013-12-05	2017-12-29	에프. 호프만-라 로슈 아게	친전자성 작용기를 갖는 헤테로아릴 피리돈 및 아자-피리돈 화합물
CN106604742B (zh)	2014-07-03	2019-01-11	百济神州有限公司	抗pd-l1抗体及其作为治疗剂及诊断剂的用途
WO2016079669A1 (fr) *	2014-11-19	2016-05-26	Novartis Ag	Dérivés d'aminopyrimidine marqués
EP3365340B1 (fr)	2015-10-19	2022-08-10	Incyte Corporation	Composés hétérocycliques utilisés comme immunomodulateurs
HUE060680T2 (hu)	2015-11-19	2023-04-28	Incyte Corp	Heterociklusos vegyületek mint immunmodulátorok
WO2017106634A1 (fr) *	2015-12-17	2017-06-22	Incyte Corporation	Dérivés de n-phényl-pyridine-2-carboxamide et leur utilisation comme modulateurs d'interactions protéine/protéine pd-1/pd-l1
EP3394033B1 (fr)	2015-12-22	2020-11-25	Incyte Corporation	Composés hétérocycliques utilisés comme immunomodulateurs
WO2017192961A1 (fr)	2016-05-06	2017-11-09	Incyte Corporation	Composés hétérocycliques utilisés comme immunomodulateurs
TW201808902A (zh)	2016-05-26	2018-03-16	美商英塞特公司	作為免疫調節劑之雜環化合物
EA202092442A3 (ru)	2016-06-07	2021-08-31	Джакобио Фармасьютикалс Ко., Лтд.	Новые гетероциклические производные, применимые в качестве ингибиторов shp2
MD3472167T2 (ro)	2016-06-20	2023-02-28	Incyte Corp	Compuși heterociclici ca imunomodulatori
CN109475536B (zh)	2016-07-05	2022-05-27	百济神州有限公司	用于治疗癌症的PD-l拮抗剂和RAF抑制剂的组合
WO2018013789A1 (fr)	2016-07-14	2018-01-18	Incyte Corporation	Composés hétérocycliques utilisés comme immunomodulateurs
WO2018033853A2 (fr)	2016-08-16	2018-02-22	Beigene, Ltd.	Forme cristalline de (s)-7-(1-acryloylpipéridin-4-yl)-2-(4-phénoxyphényle)-4,5,6,7-tétra-hydropyrazolo[1,5-a]pyrimidine-3-carboxamide, sa préparation et ses utilisations
PT3500299T (pt)	2016-08-19	2024-02-21	Beigene Switzerland Gmbh	Combinação de zanubrutinib com um anticorpo anti-cd20 ou anti-pd-1 para utilização no tratamento do cancro
US20180057486A1 (en)	2016-08-29	2018-03-01	Incyte Corporation	Heterocyclic compounds as immunomodulators
MA46285A (fr)	2016-09-19	2019-07-31	Mei Pharma Inc	Polythérapie
PE20200005A1 (es)	2016-12-22	2020-01-06	Incyte Corp	Derivados de tetrahidro imidazo[4,5-c]piridina como inductores de internalizacion pd-l1
EP3558973B1 (fr)	2016-12-22	2021-09-15	Incyte Corporation	Dérivés pyridine utilisés en tant qu'immunomodulateurs
EP3558989B1 (fr)	2016-12-22	2021-04-14	Incyte Corporation	Dérivés de triazolo[1,5-a]pyridine en tant qu'immunomodulateurs
MA47123A (fr)	2016-12-22	2021-03-17	Incyte Corp	Dérivés de benzooxazole en tant qu'mmunomodulateurs
EP3558963B1 (fr)	2016-12-22	2022-03-23	Incyte Corporation	Composés hétéroaromatiques bicycliques utilisés en tant qu'immunomodulateurs
CN110461847B (zh)	2017-01-25	2022-06-07	百济神州有限公司	(S)-7-(1-(丁-2-炔酰基)哌啶-4-基)-2-(4-苯氧基苯基)-4,5,6,7-四氢吡唑并[1,5-a]嘧啶-3-甲酰胺的结晶形式、其制备及用途
KR102317480B1 (ko)	2017-03-23	2021-10-25	자코바이오 파마슈티칼스 컴퍼니 리미티드	Shp2 억제제로서 유용한 신규한 헤테로환형 유도체
TW202515616A (zh)	2017-06-26	2025-04-16	英屬開曼群島商百濟神州有限公司	抗pd-1抗體或其抗原結合片段在製備治療用於患有肝細胞癌(hcc)之藥物的用途
CN110997677A (zh)	2017-08-12	2020-04-10	百济神州有限公司	具有改进的双重选择性的Btk抑制剂
WO2019108795A1 (fr)	2017-11-29	2019-06-06	Beigene Switzerland Gmbh	Traitement de lymphomes à cellules b indolentes ou agressives au moyen d'une combinaison comprenant des inhibiteurs de btk
PL4212529T3 (pl)	2018-03-30	2025-07-07	Incyte Corporation	Związki heterocykliczne jako immunomodulatory
HRP20230306T1 (hr)	2018-05-11	2023-05-12	Incyte Corporation	Derivati tetrahidro-imidazo[4,5-c]piridina kao pd-l1 imunomodulatori
WO2020063760A1 (fr)	2018-09-26	2020-04-02	Jacobio Pharmaceuticals Co., Ltd.	Nouveaux dérivés hétérocycliques utiles en tant qu'inhibiteurs de shp2
WO2020249001A1 (fr)	2019-06-10	2020-12-17	百济神州瑞士有限责任公司	Comprimé solide pour voie orale comprenant un inhibiteur de tyrosine kinase de bruton et son procédé de préparation
WO2021030162A1 (fr)	2019-08-09	2021-02-18	Incyte Corporation	Sels d'un inhibiteur de pd-1/pd-l1
IL291471B2 (en)	2019-09-30	2025-04-01	Incyte Corp	Pyrimido[3,2–D]pyrimidine compounds as immunomodulators
CR20220237A (es)	2019-11-11	2022-08-05	Incyte Corp	Sales y formas cristalinas de un inhibidor de pd-1/pd-l1
US11780836B2 (en)	2020-11-06	2023-10-10	Incyte Corporation	Process of preparing a PD-1/PD-L1 inhibitor
WO2022099075A1 (fr)	2020-11-06	2022-05-12	Incyte Corporation	Forme cristalline d'un inhibiteur pd-1/pd-l1
AR124001A1 (es)	2020-11-06	2023-02-01	Incyte Corp	Proceso para fabricar un inhibidor pd-1 / pd-l1 y sales y formas cristalinas del mismo
US11786531B1 (en)	2022-06-08	2023-10-17	Beigene Switzerland Gmbh	Methods of treating B-cell proliferative disorder

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA2359680A1 (fr) *	1999-01-22	2000-07-27	David M. Armistead	Inhibiteurs de kinase
JP2005255675A (ja) *	2004-02-09	2005-09-22	Tanabe Seiyaku Co Ltd	医薬組成物
US8101770B2 (en)	2004-12-16	2012-01-24	Vertex Pharmaceuticals Incorporated	Pyridones useful as inhibitors of kinases

2007
- 2007-09-10 AR ARP070103989A patent/AR063707A1/es unknown
- 2007-09-10 PE PE2007001210A patent/PE20081370A1/es not_active Application Discontinuation
- 2007-09-11 JP JP2009527626A patent/JP5563301B2/ja active Active
- 2007-09-11 AU AU2007296563A patent/AU2007296563B2/en not_active Ceased
- 2007-09-11 WO PCT/US2007/078185 patent/WO2008033857A2/fr not_active Ceased
- 2007-09-11 TW TW096133935A patent/TWI398439B/zh not_active IP Right Cessation
- 2007-09-11 EP EP07842267A patent/EP2079726B1/fr active Active
- 2007-09-11 CN CNA200780041899XA patent/CN101605778A/zh active Pending
- 2007-09-11 AT AT07842267T patent/ATE496909T1/de not_active IP Right Cessation
- 2007-09-11 ES ES07842267T patent/ES2363269T3/es active Active
- 2007-09-11 BR BRPI0716914-0A patent/BRPI0716914A2/pt not_active Application Discontinuation
- 2007-09-11 DE DE602007012281T patent/DE602007012281D1/de active Active
- 2007-09-11 KR KR1020097007473A patent/KR101444481B1/ko not_active Expired - Fee Related
- 2007-09-11 CA CA2661951A patent/CA2661951C/fr not_active Expired - Fee Related
- 2007-09-11 CL CL200702642A patent/CL2007002642A1/es unknown
- 2007-09-11 RU RU2009113692/04A patent/RU2009113692A/ru not_active Application Discontinuation
- 2007-09-11 MX MX2009002651A patent/MX2009002651A/es not_active Application Discontinuation
2009
- 2009-02-26 IL IL197264A patent/IL197264A0/en unknown
- 2009-03-06 ZA ZA200901634A patent/ZA200901634B/xx unknown
- 2009-04-01 CO CO09033749A patent/CO6180464A2/es not_active Application Discontinuation
- 2009-04-03 CR CR10709A patent/CR10709A/es unknown
- 2009-04-06 MA MA31767A patent/MA31276B1/fr unknown
- 2009-04-07 EC EC2009009238A patent/ECSP099238A/es unknown
- 2009-04-07 NO NO20091426A patent/NO20091426L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
CA2661951A1 (fr)	2008-03-20
ECSP099238A (es)	2009-07-31
ATE496909T1 (de)	2011-02-15
EP2079726B1 (fr)	2011-01-26
WO2008033857A3 (fr)	2008-06-05
KR20090074192A (ko)	2009-07-06
AR063707A1 (es)	2009-02-11
KR101444481B1 (ko)	2014-09-24
CO6180464A2 (es)	2010-07-19
RU2009113692A (ru)	2010-10-20
EP2079726A2 (fr)	2009-07-22
CL2007002642A1 (es)	2008-07-18
JP2010502750A (ja)	2010-01-28
WO2008033857A2 (fr)	2008-03-20
PE20081370A1 (es)	2008-11-28
TW200829567A (en)	2008-07-16
NO20091426L (no)	2009-06-10
MX2009002651A (es)	2009-03-26
CR10709A (es)	2009-07-14
TWI398439B (zh)	2013-06-11
ZA200901634B (en)	2009-12-30
CN101605778A (zh)	2009-12-16
AU2007296563A1 (en)	2008-03-20
ES2363269T3 (es)	2011-07-28
BRPI0716914A2 (pt)	2013-11-05
DE602007012281D1 (de)	2011-03-10
MA31276B1 (fr)	2010-04-01
IL197264A0 (en)	2009-12-24
JP5563301B2 (ja)	2014-07-30
CA2661951C (fr)	2014-11-18

Publication	Publication Date	Title
AU2007296563B2 (en)	2013-01-10	Substituted amides, method of making, and method of use thereof
AU2007296559B2 (en)	2013-01-17	Certain substituted amides, method of making, and method of use thereof
US7838523B2 (en)	2010-11-23	Certain substituted amides, method of making, and method of use thereof
AU2009244291B2 (en)	2014-02-13	Substituted amides, method of making, and use as Btk inhibitors
AU2006223409B2 (en)	2011-07-21	Certain substituted amides, method of making, and method of use thereof
US20080125417A1 (en)	2008-05-29	Certain pyrimidines, method of making, and method of use thereof
EP1812442A2 (fr)	2007-08-01	Certaines imidazo[1,2-a] pyrazin-8-ylamines et les procédés de fabrication et d'utilisation correspondants
WO2010068806A1 (fr)	2010-06-17	Dérivés amides utilisés comme inhibiteurs de la btk dans le traitement des affections allergiques, auto-immunes et inflammatoires et dans le traitement du cancer

Legal Events

Date	Code	Title	Description
2009-04-23	DA3	Amendments made section 104	Free format text: THE NATURE OF THE AMENDMENT IS: AMEND THE O-INVENTOR NAME FROM LEE, TONY TO LEE, SEUNG H.
2013-05-09	FGA	Letters patent sealed or granted (standard patent)
2022-04-07	MK14	Patent ceased section 143(a) (annual fees not paid) or expired